Bucket List guide to Chicago

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Knocking off Bucket-List items in the Windy City

As professional travelers, we are frequently asked, “What’s your favorite destination?” Of course, we find it impossible to answer that question. Every place we visit becomes a part of us in its own special way. It’s like asking me to chose between wine and bacon, or asking Sandi to choose between coffee and cookies. The question is simply too broad.


Still, if you were to ask me to choose my favorite destination in the United States for checking things off your Bucket List, I would answer, “Chicago!” The city is layered enough with history, architecture, sports, shopping, art, museums, parks, and food to keep Bucket List enthusiasts engaged for days.

Whether you’re a Bucket List veteran or virgin, Chicago has something worthy of your interest. Here are some of our suggestions to guide you on your quest. Just don’t ask us to pick a favorite.


Visit the SkyDeck at Willis (Sears) Tower

When the Sears Tower opened in 1974, it was the tallest building in the world. Today it is called the Willis Tower and offers some of the most spectacular views of Chicago and Lake Michigan from its SkyDeck. For an extra thrill (and an extra wait in line) you can step out on to one of the retractable glass balconies suspended 103 stories above South Wacker Drive.

Catch a Cubs game at

Wrigley field Chicago


Even if you’re not a baseball fan, you’re sure to have a blast at the iconic Wrigley field. The park is the second-oldest ball park in the major leagues. This, combined with the passion of Cubs fans makes any visit an for an unforgettable experience. Though the Cubs haven’t won a World Series since 1908, Cub pride is prevalent in the neighborhood as businesses and fans alike adorn themselves in Cubs paraphernalia. You even can see fans watching the games from rooftops of buildings outside the stadium walls. As a Bucket-List bonus, you’ll want to eat a Chicago style hot-dog while at the game. Or drink Old-Style beer.


Categories: Abacos, Chicago, Illinois, USA

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